Questions tagged [organoboron-compounds]
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How to interpret molecular orbital (HOMO - LUMO) plots in Chem3D 22.0?
Recently, I have been trying to understand the origin of the difference in reactivity of alkynyl-boron(ate) complexes so I tried to generate a molecular orbital plot on Chem3D (Version 22.0.22 64bit) ...
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Is it possible to make a carbon icosahedron?
Cyclopentadienyl $\ce{C5H5^-}$ is a hydrocarbon anion with a 5 fold symmetry. The carbon atoms can be replaced with nitrogen, oxygen, sulfur, etc. to yield diverse aromatic 5-membered rings. For ...
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Does boric acid really rearrange phenols?
This reaction was on prepchem.com and I want to know whether it could work. Most of their reactions are well sourced but this is rather scant (and can't find the patent referenced).
It is possible ...
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In hydroboration oxidation reaction .. why do not we use sodium hydroxide alone as a nuclophile?
Why do not we use sodium hydroxide alone as a nuclophile instead of using hydrogen peroxide along with sodium hydroxide
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Hydroboration–oxidation reaction without THF
The first step of hydroboration–oxidation usually involves $\ce{BH3}$ accompanied by THF. Is it possible for hydroboration to occur without the presence of THF? Borane is incredibly reactive. Wouldn't ...
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Purpose of "1H" in naming of substituted heterocyclic compouns [duplicate]
I had a curious thought about the following molecule's name:
For such a simple molecule it seemed awfully complicated. From what I gathered, the "[c][1,2]oxaborinin-1-ol" stems from the ...
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Regioselectivity of hydroboration-oxidation of enol ethers
In the book Hydroboration and Organic Synthesis, on p. 99, it is written that:
hydroboration [of enol ethers] proceeds regioselectively, placing essentially all of the boron atoms at the β position
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Hydroboration, steroselectivity and anti-markovnikov product [duplicate]
My first question has to do with the fact that Hydroboration produces an anti-markovnikov product, why?. I don't see how that happens. A wikipedia artical says that B has a partial positive charge ...
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I need to reduce the Nitrile group without affecting the boronic acid. How to do that?
I need to Reduce the Nitrile group (CN) in the (3-cyanophenyl)boronic acid in to a primary amine without disturbing the Boronic acid group.Using LAH can trigger reduction of Boronic group. what are my ...
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What is the mechanism for the reaction of alkenes with diborane and chloramine?
$$\ce{CH3-CH=CH2 ->[B2H6/THF][NH2Cl/H2O, Δ] Product (P)}$$
What is $\ce{Product (P)}?$
First of all, in this reaction I performed hydroboration to form an alkylborane. But I don't have any ideas ...
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Stereoselectivity of Roush crotylboration
One can use a tartrate derived boronate to enact enantioselective crotyl transfer. Eg in scheme below:
I do not understand how the stereoselectivity arises. We have a chiral boronate, true, and we ...
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Rationalise the Relative Reactivity of Borane and DIBAL as Reductants
In Clayden's Organic Chemistry (Second Edition) it is written that borane is useful in chemoselectively reducing the most nucleophilic carbonyl to its corresponding alcohol. It is later said that ...
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What happens when an alkylborane is treated with acetic acid?
In the hydroboration reactions of alkenes I've seen so far, they were always followed by oxidation with $\ce{H2O2/NaOH}$ (to yield alcohols).
Today I found a peculiar reaction in which acetic acid-...
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Why is an alkoxide released instead of hydroxide in the attack of trialkyloxyborane by hydroxide?
In the mechanism of a hydroboration-oxidation, the oxidation part includes a nucleophilic attack of a hydroxide on a trialkyloxyborane ( $\ce{B(OR)_3}$ where $\ce{R}$ is an alkyl group).
It creates ...
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Why does boron add to the less substituted carbon in the hydroboration of an alkene?
In the hydroboration of a typical alkene, the boron fragment ends up attached to the less substituted carbon:
What are the electronic or steric factors that lead to this regioselectivity?
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